US4235731A - Modified terpolymer dispersant - VI improver - Google Patents

Modified terpolymer dispersant - VI improver Download PDF

Info

Publication number
US4235731A
US4235731A US05/733,575 US73357576A US4235731A US 4235731 A US4235731 A US 4235731A US 73357576 A US73357576 A US 73357576A US 4235731 A US4235731 A US 4235731A
Authority
US
United States
Prior art keywords
terpolymer
oil
maleic anhydride
sub
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US05/733,575
Other languages
English (en)
Inventor
Thomas E. Kiovsky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell USA Inc
Original Assignee
Shell Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US05/733,575 priority Critical patent/US4235731A/en
Priority to BE1008425A priority patent/BE859472A/nl
Priority to JP12362077A priority patent/JPS5350292A/ja
Priority to FR7731154A priority patent/FR2367781A1/fr
Priority to GB43080/77A priority patent/GB1548525A/en
Priority to DE19772746549 priority patent/DE2746549A1/de
Priority to NL7711351A priority patent/NL7711351A/nl
Application granted granted Critical
Publication of US4235731A publication Critical patent/US4235731A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/02—Polyethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • C08F255/06—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms on to ethene-propene-diene terpolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/14—Esterification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/022—Ethene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/32—Esters of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/12—Polysaccharides, e.g. cellulose, biopolymers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • 3,864,268 may improve both dispersancy and viscosity characteristics over a narrow range, by employing an oxidation step to attach polar groups to the polymer backbone the patentees have reduced lubricant stability by introducing sites for oxidative attack.
  • the lubricant additive disclosed in U.S. Pat. No. 3,842,010 lacks a certain amount of oxidative stability due to the employment of an epoxidation step to attach polyamine groups to the polymer backbone.
  • a new lubricant additive having both dispersant and viscosity-index improving properties as well as good oxidative stability has now been found.
  • Ashless, oil-soluble additives having both dispersant and viscosity-index (VI) improving properties are prepared by the process comprising:
  • step (b) reacting the product of step (a) with a C 1 to C 18 amine containing 1 to 8 nitrogen atoms.
  • TEPA tetraethylene pentamine
  • the terpolymer employed as the starting material need not be of the ultimate desired molecular weight range of 70,000 to 150,000. If desired, terpolymers having molecular weights of 150,000 to 1,000,000 may also be employed. As part of the present invention, the derivatized terpolymer of higher than desird molecular weight may be subjected to a shearing process as hereinafter described to reduce the molecular weight and improve molecular weight distribution to the desired range.
  • terpolymers employed in the instant invention are well known.
  • ethylene-propylene-non-conjugated diolefin terpolymers are well known articles of commerce.
  • the preparation of typical terpolymers, using Ziegler-Natta catalysts, is described for example in U.S. Pat. Nos. 2,933,480; 3,000,866; and 3,093,621.
  • These terpolymers, which are primarily produced for use in elastomeric compositions, are characterized by the absence of chain or backbone unsaturation and contain sites of unsaturation in groups which are pendant to or are in cyclic structures outside of the main polymer chain. These structures render the polymers particularly resistant to breakdown by atmospheric oxidation or ozone.
  • Useful terpolymers for the production of the derivatized products of this invention comprise ethylene, a C 3 to C 8 straight or branched chain alpha-olefin and a non-conjugated diene.
  • Representative non-limiting examples of non-conjugated dienes that may be used as the third monomer in the terpolymer include:
  • Branched chain acyclic dienes such as: 5-methyl-1, 4-hexadiene; 3,7-dimethyl 1,6-octadiene; 3,7-dimethyl 1,7-octadiene; and the mixed isomers of dihydro-myrcene and dihydrocimene.
  • (c) Single ring alicyclic dienes such as: 1,4-cyclohexadiene; 1,5-cyclooctadiene; 1,5-cyclododecadiene, 4-vinyl-cyclohexene; 1-allyl,4-isopropylidene cyclohexane; 3-allyl-cyclopentene; 4-allyl cyclohexene and 1-isopropenyl 4-(4-butenyl) cyclohexane.
  • Multi single ring alicyclic dienes such as: 4,4'-di-cyclopentenyl and 4,4'-dicyclohexenyl dienes.
  • Multi-ring alicyclic fused and bridged ring dienes such as: tetrahydroindene; methyl tetrahydroindene; dicyclopentadiene; bicyclo(2.2.1) hepta 2,5-diene; alkenyl, alkylidene, cycloalkenyl and cycloalkylidene norbornenes such as: 5-methylene-6-methyl-2-norbornene; 5-methylene-6,6-dimethyl-2-norbornene; 5-propenyl-2-norbornene; 5-(3-cyclopentenyl)-2-norbonene and 5-cyclohexyldene-2-norbornene.
  • terpolymers contain non-conjugated dienes having 5 to 14 carbon atoms and exhibit weight average molecular weights of from 70,000 to 1,000,000 e.g., 70,000 to 150,000.
  • Preferred dienes include ethylidene norbornene, dicyclopentadiene and 1,4 hexadiene.
  • the terpolymers suitable for conversion to the succinimides and their functional adducts of the present invention may be illustrated for various non-conjugated diene monomers as random terpolymers in which the following moieties are linked in the polymer chain in a random sequence and in a varying number.
  • x, y and z are cardinal numbers. While these terpolymers are essentially amorphous in character by superficial inspection, they may contain up to about 25 percent by weight of crystalline segments as determined by X-ray or differential scanning calorimetry. Details of these methods for measurement of crystallinity are found in J. Polymer Science, A-2, 9, 127 (1971) by G. Ver Strate and Z. W. Wilchinsky.
  • Terpolymers useful in the present invention contain at least 30 mol. percent, preferably not more than 85 mol. percent of ethylene; between about 15 and about 70 mol. percent of a higher alphaolefin or mixture thereof, preferably propylene; and between 1 and 20 mol. percent, preferably 1 to 15 mol. percent, of a non-conjugated diene or mixture thereof.
  • the terpolymer is first reacted with maleic anhydride in the presence of a solvent.
  • the maleic anhydride reacts with the double bonds available on the diene portion of the terpolymer.
  • about 10 to 100%, preferably 50 to 95% of the double bonds in the terpolymer are converted to succinic anhydride groups. Since it is uneconomical for practical purposes to attempt to convert all of the double bonds in the terpolymer molecule to anhydride groups, the structure of the resulting maleated polymer will typically contain some unreacted double bonds.
  • solvents may be employed in the maleation step including generally olefin-free petroleum hydrocarbons, aromatics and halogenated hydrocarbons.
  • a preferred solvent is a lubricating oil basestock.
  • Another useful solvent is trichlorobenzene.
  • a concentration in the range of about 1 to 10 percent by weight of terpolymer in solvent may conveniently be used for maleation.
  • maleic anhydride over that stoichiometrically necessary to react with all the double bonds present in the diene portion of the terpolymer is typically employed.
  • at least one mole of maleic anhydride is used for each mole of diene monomer present in the terpolymer, with molar ratios of maleic anhydride to diene of between about 1:1 and 2:1 being particularly suitable. Less than stoichiometric amounts of maleic anhydride may also be used.
  • the maleation may occur with or without the use of catalyst or radical initiators such as tertiary hydroperoxide.
  • catalyst or radical initiators such as tertiary hydroperoxide.
  • the temperature is typically maintained between about 180° and 250° C. for between about 1 hour and about 10 hours. Typical conditions are about 225° C. for about 4 hours. Any excess maleic anhydride is typically removed by either vacuum distillation or through the use of a stripping gas stream.
  • the maleation takes place in the presence of chlorine.
  • Chlorination has been disclosed with polymers of isobutene in U.S. Pat. No. 949,981.
  • the molar amount of chlorine used is preferably such that the mixture of polymer and maleic anhydride is contacted with from 0.3 to 1.5, more preferably from 0.5 to 1.2 moles of chlorine for each mole of maleic anhydride. Insofar as the conversion of the polymer is concerned there appears to be no lower limit on the amount of chlorine which may be used. In practice, however, it is preferred to remain within the aforesaid ranges.
  • the mixture of polymer and maleic anhydride is heated to the reaction temperature before it is contacted with the chlorine.
  • the mixture is contacted with a molar deficiency of chlorine before any substantial amount, e.g. less than half, of the maleic anhydride has reacted.
  • substantially none of the maleic anhydride has reacted.
  • the rate of introduction of chlorine into the mixture may vary between wide limits but is preferably such that it equals the rate of chlorine uptake.
  • the chlorine is introduced over a period of from 0.5 to 10 hours, preferably of from 3 to 7 hours, at a temperature of between about ambient to 100° C.
  • the resultant product mixture is advantageous to subject the resultant product mixture to a post-reaction or thermal treatment.
  • This thermal treatment is suitably carried out at a temperature in the range of from 140° to 220° C., preferably from 160° to 210° C.
  • the conditions are usually such, e.g. reflux conditions, that substantially no part of the product mixture is removed during this thermal treatment.
  • the thermal treatment may be for 0.1 to 20 hours but is preferably from 0.5 to 10 hours. Longer periods tend to increase the formation of tarry by-products.
  • the maleated polymer is then reacted with a polyamine to form the oil-soluble product of the instant invention.
  • the C 1 to C 18 amines employed in the instant invention can be branched or unbranched, saturated, aliphatic, primary or secondary amines, containing 1 to 8 nitrogens, preferably mono or diamines, such as ethyl amine, butylamine, sec. butylamine, diethylamine, etc., but including higher polyamines such as alkylene polyamines, wherein pairs of nitrogen atoms are joined by alkylene groups of 2 to 4 carbon atoms.
  • n 2 to 4 and m is 0 to 6.
  • polyamines include tetraethylene pentamine, tripropylene tetramine, N-aminoalkyl piperazines, e.g., N-(2-aminoethyl) piperazine, N,N'-di(2-aminoethyl) piperazine, etc.
  • Preferred is tetraethylene pentamine, as well as corresponding commercial mixtures such as "Polyamine H", and "Polyamine 500".
  • the molar ratio of polyamine to diene portion of the terpolymer is typically between about 0.1:1 and about 2:1, preferably between about 0.5 and about 2:1, most preferably about 1:1.
  • the conditions during amidization are typically about 150° to 250° C. for between about 1 hour and 5 hours, e.g. about 1 hour at 160° C. followed by 1 hour at 190° C.
  • excess polyamine is employed, then it may be desirable to remove the excess.
  • One means of doing this is to first add a volume of heptane equal to the volume of dissolved additive. Then an equal volume of methanol is added. Two separate layers are therein formed; a bottom layer comprising predominantely methanol and the unreacted polyamine and a top layer comprising predominantely heptane, the solvent and the additive product. After separating the bottom layer, the volatiles present in the top layer can then be removed by a distillation technique.
  • the terpolymer originally employed had a sufficiently low molecular weight, e.g. between about 70,000 and about 150,000, then the final additive product should have sufficient viscosity-index improving properties.
  • the instant additive product starting with a terpolymer having a high molecular weight between about 200,000 and about 1,000,000.
  • One shearing mechanism involves adding a solvent such as heptane to the additive product in order to reduce the viscosity, and then pumping the solution through a Diesel injecton nozzle at high pressures, such as above about 1000 psig.
  • Other high shear devices include high shear mixers and pumps such as a gear pump.
  • the molecular weight of the resulting polymer can be controlled by varying the number of times that the solution is pumped through the nozzle or high shear device.
  • shearing also narrows the molecular weight distribution since bigger molecules are sheared more readily than smaller molecules. This narrower molecular weight distribution is advantageous since it results in greater stability in the engine. It is preferred that the ratio of M w /M n be between about 1 and about 4 where M w is the weight average molecular weight and M n is the number average molecular weight.
  • the reaction product of this invention can be incorporated in lubricating oil compositions, e.g., automotive crankcase oils, in concentrations within the range of about 0.1 to about 15, preferably about 0.1 to 3, weight percent based on the weight of the total compositions.
  • lubricating oils to which the additives of the invention can be added include not only mineral lubricating oils, but synthetic oils also.
  • Synthetic hydrocarbon lubricating oils may also be employed, as well as non-hydrocarbon synthetic oils including dibasic acid esters such as di-2-ethyl hexyl sebacate, carbonate esters, phosphate esters, halogenated hydrocarbons, polysilicones, polyglycols, glycol esters such as C 13 oxo acid diesters of tetraethylene glycol, etc.
  • dibasic acid esters such as di-2-ethyl hexyl sebacate
  • carbonate esters phosphate esters, halogenated hydrocarbons, polysilicones, polyglycols, glycol esters such as C 13 oxo acid diesters of tetraethylene glycol, etc.
  • compositions of concentrates other conventional additives may also be present, including dyes, pour point depressants, antiwear agents, e.g., tricresyl phosphate, zinc dialkyl dithiophosphates of 3 to 8 carbon atoms, antioxidants such as phenyl-alpha-naphthylamine, tert. octylphenol sulfide, bis-phenols such as 4,4'-methylene bis(3,6-di-tert.
  • antiwear agents e.g., tricresyl phosphate, zinc dialkyl dithiophosphates of 3 to 8 carbon atoms
  • antioxidants such as phenyl-alpha-naphthylamine, tert. octylphenol sulfide, bis-phenols such as 4,4'-methylene bis(3,6-di-tert.
  • viscosity index improvers such as the ethylene-higher olefin copolymer, polymethylacrylates, polyisobutylene, alkyl fumarate-vinyl acetate copolymers, and the like as well as other ashless dispersants or detergents such as overbased sulfonates.
  • Embodiment I various terpolymers are employed to form ashless dispersants and VI improvers for lubricating oils.
  • the higher alpha-olefin component of the terpolymer was propylene and the polyamine employed was tetraethylene pentamine (TEPA).
  • TEPA tetraethylene pentamine
  • the terpolymer was dissolved in a standard HVI 100 Neutral lubricating oil base stock resulting in a 5 to 10% weight solution. Then an approximately two-fold excess of maleic anhydride was added to the solution, i.e., the stoichiometric amount of maleic anhydride theoretically necessary to react with all the double bonds available on the diene portion of the terpolymer was doubled.
  • the maleation step was carried out by heating the reactants at 225° C. for four hours under a nitrogen blanket in the absence of any added catalyst. Any unreacted maleic anhydride was removed by vacuum distillation at about 200° C.
  • the product solution was then washed with a volume of methanol equal to the volume of heptane employed.
  • the heptane-oil-additive product layer was then separated. Then the volatiles (mainly heptane and methanol) were vacuum distilled at about 150° C.
  • the resulting additive product was then further diluted with sufficient 100 HVI oil to give a 2% by weight polymer in oil lubricating composition.
  • Effectiveness as a sludge dispersant was assessed by means of three commonly used bench tests: a carbon black dispersancy test (CBT) in which the minimum amount of dispersant required to keep carbon black dispersed in oil is determined, a Spot Dispersancy Test (SDT) in which one measures the ability of given concentration of dispersant to facilitate movement of suspended sludge on blotter paper, and the General Motors Oxidation Test (GMOT), in which one measures the ability of the dispersant to reduce the rate of formaton of sludge when air is passed through the hot oil-dispersant solution.
  • CBT carbon black dispersancy test
  • SDT Spot Dispersancy Test
  • GMOT General Motors Oxidation Test
  • Stability for 100 hours can be considered a good result.
  • Spot Dispersancy Test one part of a 2% weight polymer solution in 100 N oil is mixed with two parts used VC oil and heated overnight at 150° C. Blotter spots are then made on filter paper and the ratio of sludge spot diameter to oil spot diameter is measured after 24 hours. A poor value is under about 50% and a good value is 60% or greater.
  • a sequence V-C Engine Test was performed employing the oil-soluble product designated Run No. 1 in Illustrative Embodiment I.
  • the V-C Engine Test is an ASTM test procedure designated to evaluate the sludge and varnish forming tendencies of motor oils.
  • the oil formulation employed in the test comprised 35 parts by weight of the oil-soluble product of Run No. 1 (IEI), 45.5 parts by weight of a 250 neutral high viscosity index lubricating oil, 16.4 parts by weight of a 100 neutral high viscosity index lubricating oil, and a typical dispersant inhibitor package. No additional dispersants or VI improvers were added.
  • the resulting oil formulation had a V K at 210° F. of about 21 centistokes and a 0° F. viscosity of about 21 poise.
  • Table III The results of the test are presented below in Table III along with the minimum SE service classification.
  • Illustrative Embodiment III indicates the effect of shearing on molecular weight distribution.
  • the starting terpolymer was EPsyn 4506 and had a weight average molecular weight of about 195,000.
  • This terpolymer was sheared by being passed through a Diesel injection nozzle a number of times.
  • the final terpolymer had a molecular weight of about 90,000 and a Q value of about 1.43.
  • This embodiment illustrates that shearing according to the present invention not only reduces molecular weight to the desired range, but also has an excellent effect on molecular weight distribution.
  • Illustrative Embodiment V shows the effect of varying the ratio of polyamine to diene.
  • the terpolymer employed was EPsyn 40 A.
  • 10 grams of terpolymer was first chlorinated and then reacted with 0.8 grams of maleic anhydride. Then the maleated terpolymer was reacted with varying amounts of TEPA.
  • the amounts of TEPA employed and the test results are presented below in Table IV.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US05/733,575 1976-10-18 1976-10-18 Modified terpolymer dispersant - VI improver Expired - Lifetime US4235731A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US05/733,575 US4235731A (en) 1976-10-18 1976-10-18 Modified terpolymer dispersant - VI improver
BE1008425A BE859472A (nl) 1976-10-18 1977-10-07 Gemodificeerd terpolymeer als v.i.-verbeterend dispergeermiddel
JP12362077A JPS5350292A (en) 1976-10-18 1977-10-17 Improver of dispersion properties and viscosity index for modified terpolymers
FR7731154A FR2367781A1 (fr) 1976-10-18 1977-10-17 Terpolymere modifie utilisable comme additif dispersant et ameliorant l'indice de viscosite
GB43080/77A GB1548525A (en) 1976-10-18 1977-10-17 Terpolymer dispersant vi improver
DE19772746549 DE2746549A1 (de) 1976-10-18 1977-10-17 Oelloesliches produkt und seine verwendung
NL7711351A NL7711351A (nl) 1976-10-18 1977-10-17 Gemodificeerd terpolymeer als v.i.-verbeterend dispergeermiddel.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/733,575 US4235731A (en) 1976-10-18 1976-10-18 Modified terpolymer dispersant - VI improver

Publications (1)

Publication Number Publication Date
US4235731A true US4235731A (en) 1980-11-25

Family

ID=24948210

Family Applications (1)

Application Number Title Priority Date Filing Date
US05/733,575 Expired - Lifetime US4235731A (en) 1976-10-18 1976-10-18 Modified terpolymer dispersant - VI improver

Country Status (2)

Country Link
US (1) US4235731A (nl)
BE (1) BE859472A (nl)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2423530A1 (fr) * 1978-04-17 1979-11-16 Lubrizol Corp Compositions d'additifs a buts multiples pour compositions lubrifiantes et concentres les contenant
US4357250A (en) * 1978-04-17 1982-11-02 The Lubrizol Corporation Nitrogen-containing terpolymer-based compositions useful as multi-purpose lubricant additives
US4505834A (en) * 1980-10-27 1985-03-19 Edwin Cooper, Inc. Lubricating oil compositions containing graft copolymer as viscosity index improver-dispersant
US4749505A (en) * 1985-07-08 1988-06-07 Exxon Chemical Patents Inc. Olefin polymer viscosity index improver additive useful in oil compositions
US5427702A (en) * 1992-12-11 1995-06-27 Exxon Chemical Patents Inc. Mixed ethylene alpha olefin copolymer multifunctional viscosity modifiers useful in lube oil compositions
US5674819A (en) * 1995-11-09 1997-10-07 The Lubrizol Corporation Carboxylic compositions, derivatives,lubricants, fuels and concentrates
RU2684412C1 (ru) * 2017-11-02 2019-04-09 Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") Депрессорно-диспергирующая присадка к дизельному топливу, способ ее получения и способ получения депрессорного и диспергирующего компонентов депрессорно-диспергирующей присадки

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3219666A (en) * 1959-03-30 1965-11-23 Derivatives of succinic acids and nitrogen compounds
US3235503A (en) * 1963-03-28 1966-02-15 Chevron Res Lubricant containing alkylene polyamine reaction product
US3329658A (en) * 1962-05-14 1967-07-04 Monsanto Co Dispersency oil additives
US3432479A (en) * 1965-10-07 1969-03-11 Sinclair Research Inc Reaction product of monoamine,polyamine and polymer of a monovinyl monomer and maleic anhydride
US3438899A (en) * 1968-02-23 1969-04-15 Chevron Res Alkenyl succinimide of tris (aminoalkyl) amine
US3471458A (en) * 1966-12-16 1969-10-07 Chevron Res Polyimides of olefin-maleic anhydride copolymers as diesel fuel additives
US3541012A (en) * 1968-04-15 1970-11-17 Lubrizol Corp Lubricants and fuels containing improved acylated nitrogen additives
US3620977A (en) * 1968-12-17 1971-11-16 Chevron Res Reaction product of alkylene polyamines and chlorinated alkenyl succinic acid derivatives
US3864270A (en) * 1973-07-09 1975-02-04 Texaco Inc Dehydrohalogenated Polyalkene-Maleic Anhydride Reaction
US3941808A (en) * 1969-01-29 1976-03-02 Atlantic Richfield Company Product
US4169063A (en) * 1977-03-11 1979-09-25 Shell Oil Company EPR dispersant VI improver

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3219666A (en) * 1959-03-30 1965-11-23 Derivatives of succinic acids and nitrogen compounds
US3341542A (en) * 1959-03-30 1967-09-12 Lubrizol Corp Oil soluble acrylated nitrogen compounds having a polar acyl, acylimidoyl or acyloxy group with a nitrogen atom attached directly thereto
US3329658A (en) * 1962-05-14 1967-07-04 Monsanto Co Dispersency oil additives
US3235503A (en) * 1963-03-28 1966-02-15 Chevron Res Lubricant containing alkylene polyamine reaction product
US3432479A (en) * 1965-10-07 1969-03-11 Sinclair Research Inc Reaction product of monoamine,polyamine and polymer of a monovinyl monomer and maleic anhydride
US3471458A (en) * 1966-12-16 1969-10-07 Chevron Res Polyimides of olefin-maleic anhydride copolymers as diesel fuel additives
US3438899A (en) * 1968-02-23 1969-04-15 Chevron Res Alkenyl succinimide of tris (aminoalkyl) amine
US3541012A (en) * 1968-04-15 1970-11-17 Lubrizol Corp Lubricants and fuels containing improved acylated nitrogen additives
US3620977A (en) * 1968-12-17 1971-11-16 Chevron Res Reaction product of alkylene polyamines and chlorinated alkenyl succinic acid derivatives
US3941808A (en) * 1969-01-29 1976-03-02 Atlantic Richfield Company Product
US3864270A (en) * 1973-07-09 1975-02-04 Texaco Inc Dehydrohalogenated Polyalkene-Maleic Anhydride Reaction
US4169063A (en) * 1977-03-11 1979-09-25 Shell Oil Company EPR dispersant VI improver

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2423530A1 (fr) * 1978-04-17 1979-11-16 Lubrizol Corp Compositions d'additifs a buts multiples pour compositions lubrifiantes et concentres les contenant
US4357250A (en) * 1978-04-17 1982-11-02 The Lubrizol Corporation Nitrogen-containing terpolymer-based compositions useful as multi-purpose lubricant additives
US4505834A (en) * 1980-10-27 1985-03-19 Edwin Cooper, Inc. Lubricating oil compositions containing graft copolymer as viscosity index improver-dispersant
US4749505A (en) * 1985-07-08 1988-06-07 Exxon Chemical Patents Inc. Olefin polymer viscosity index improver additive useful in oil compositions
US5427702A (en) * 1992-12-11 1995-06-27 Exxon Chemical Patents Inc. Mixed ethylene alpha olefin copolymer multifunctional viscosity modifiers useful in lube oil compositions
US5744429A (en) * 1992-12-11 1998-04-28 Exxon Chemical Patents Inc Mixed ethylene alpha olefin copolymer multifunctional viscosity modifiers useful in lube oil compositions
US5674819A (en) * 1995-11-09 1997-10-07 The Lubrizol Corporation Carboxylic compositions, derivatives,lubricants, fuels and concentrates
RU2684412C1 (ru) * 2017-11-02 2019-04-09 Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") Депрессорно-диспергирующая присадка к дизельному топливу, способ ее получения и способ получения депрессорного и диспергирующего компонентов депрессорно-диспергирующей присадки

Also Published As

Publication number Publication date
BE859472A (nl) 1978-04-07

Similar Documents

Publication Publication Date Title
US4632769A (en) Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
US4156061A (en) Epoxidized terpolymer or derivatives thereof, and oil and fuel compositions containing same
EP0145369B1 (en) Ethylene copolymer viscosity index improver - dispersant additive useful in oil compositions
EP0066953B1 (en) Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
US4169063A (en) EPR dispersant VI improver
EP0352072B1 (en) Improver end-capped multifunctional viscosity improver
EP0295853B1 (en) Ethylene copolymer viscosity index improver dispersant additive useful in oil compositions
US3842010A (en) Oil and fuel compositions containing epoxidized terpolymer derivatives
US4089794A (en) Polymeric additives for fuels and lubricants
US4032700A (en) Process for the preparation of aminated polymers useful as additives for fuels and lubricants
EP0336716B1 (en) Lactone modified viscosity modifiers useful in oleaginous compositions
EP0087234B1 (en) Ashless dispersant compounds, their preparation, and their use in providing dispersancy in lubricating oils or liquid fuels
US4033889A (en) Terpolymer dispersant - VI improver
US4715975A (en) Oil containing dispersant VII olefin copolymer
US5094766A (en) Dispersant-antioxidant viscosity index improver
EP0352070A1 (en) Improved multifunctional viscosity index improver
US4235731A (en) Modified terpolymer dispersant - VI improver
US4098710A (en) Oil-soluble addition products of an ethylene-propylene copolymer and anionically polymerizable monomer having utility as multifunctional V.I. improver for lubricating oils
US4194984A (en) Ethylene copolymer/ethylenically unsaturated nitrogen reactant ene adducts having utility as multifunctional V. I. improvers for lubricating oils
EP0295854B1 (en) Stabilised grafted ethylene copolymer additive useful in oil compositions
EP0369674B1 (en) Improved multifunctional viscosity index improver
CA1099047A (en) Epr dispersant vi improver
US4769043A (en) Oil containing dispersant VII olefin copolymer
EP0365550B1 (en) Composition comprising nitrogen-containing hydrocarbon adducts
US5135671A (en) Multifunctional viscosity index improver containing units from unsaturated chlorides and aromatic amines